Fly to Ushuaia and ride to Alaska on a 2023 Aprilia Tuareg 660. Easy peasy.
I researched a great new ADV midsize bike, decided on the Aprilia, with real cruise control and tubeless tires. I then spent time researching how best to equip it. Even though I rode it down to here from the USA, it only has 12k kilometers on it, which will be about 15k by when Ireturn to Ushuaia. Many farkles including skid plate, crash bars, heated grips, and racks with soft, lockable panniers, rear luggage rack, Scott steering damper, Quadlock cell holder with charging and vibration dampener, taller windscreen, highway pegs, cruise control, tubeless tires, slipper clutch, Doubletake mirrors, fork covers, tire pressure monitoring system, helmet lock, heel shifter, quick shifter, tank bag, BRP hand guards, mesh seat cover, wrist rest, stash container, Iron Butt Association license plate frame, and handicapped plate. Optional additions include a modular helmet, duffle bag, tools, Klim jacket and pants, a Helite airbag backpack, and front and rear cameras.
Even though this is a wonderful road and dirt bike, I have not ridden it off road as i do not have the skills. I will replace the soon-to-be worn stock rear tire with however aggressive a tire that you would like. Clear title, registration, and handicapped plate with Iron Butt frame.
$15+k invested and will sell for $10k firm.

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motomon at pobox dot com
Have returned to Latin America ... again in 2020.